Shailene Woodley has been spotted enjoying a new romantic connection with British actor Milo Callaghan in Milan, as the pair walked together during the bustling Milan Fashion Week on February 25, 2026. The 34-year-old actress, known for her roles in various acclaimed films and series, has recently transitioned from a relationship with Lucas Bravo, the star of ‘Emily in Paris,’ with whom she split in September 2025 after approximately six months of dating.
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Photographers captured moments of the new couple strolling arm-in-arm through the fashionable streets of Milan, a city renowned for its style and artistic flair. In various images, Woodley appeared affectionate towards Callaghan, placing her hand on the back of his jeans as they enjoyed each other’s company. Such displays of intimacy suggest that the pair is growing close amidst the glamour and excitement of the fashion event.
Lucas Bravo had been Woodley’s most recent romantic partner, with their relationship confirmed by PEOPLE back in March 2025. However, news of their separation emerged six months later, with sources revealing that the couple parted on amicable terms. A source disclosed that their romance had been “a breath of fresh air for her,” hinting at its positive impact on Woodley during its duration. Yet, it appears that diverging priorities ultimately led to their breakup.
As Woodley explores this new chapter with Callaghan, the British actor is making a name for himself in the entertainment industry. Callaghan, aged 28, made his television debut in 2020 and has since appeared in notable projects including the Starz series ‘The Spanish Princess’ and the legal drama ‘The Rainmaker,’ which aired on USA Network in 2025. His versatility has been showcased in various roles, notably featuring alongside rising stars such as Madelaine Petsch in the horror flick ‘The Strangers.’
In addition to her romantic pursuits, Woodley continues to flourish in her professional life. Recently, she starred in the 2025 film ‘Motor City’ and has taken the lead in the second season of Hulu’s thriller series ‘Paradise,’ which debuted on February 23, 2026. Furthermore, the actress remains dedicated to a longstanding passion project—a biopic about the iconic 1960s rock singer Janis Joplin, a venture she has been developing for over seven years.
Despite her recent split from Bravo, Woodley remains focused on her career and personal growth, seamlessly balancing her professional commitments and budding romance with Callaghan. The couple’s public appearance in Milan suggests they are enjoying their time together while navigating their respective careers in the competitive entertainment landscape.
As the dust settles from her previous relationship, it seems that Woodley is hopeful about this new chapter. Both actors are at pivotal points in their careers, with the world of cinema and television rapidly evolving around them. Whether this romance with Callaghan will flourish remains to be seen, but their affectionate outing in Milan has certainly caught the attention of fans and onlookers alike.
In the constantly changing world of celebrity relationships and projects, it will be interesting to see how Woodley and Callaghan navigate their personal and professional lives moving forward. As they enjoy their time together amidst the backdrop of fashion and culture, supporters of both actors will likely be watching closely for updates on their journey together.